Fatty acid carriers for synthetic peptides

Abstract

A synthetic vaccine is contemplated comprising a peptide residue coupled to one or more alkyl or alkenyl groups of at least 12 carbon atoms or other lipophilic substance wherein said peptide residue contains a sequence of 6 amino acids corresponding to the sequence of such amino acids in a protein antigen or allergen where the greatest local average hydrophilicity of the antigen or allergen is found.

What is claimed is: 
     
       1. A synthetic antigen comprising a carrier coupled to a peptide residue, (a) the peptide residue having an N terminal amino group and a C terminal carboxy group, said peptide residue comprising a naturally occurring sequence of at least six amino acids, said peptide residue containing an epitope and being coupled to the carrier which comprises   (b) one or more alkyl or alkenyl fatty acid groups having at least 12 carbon atoms, said coupling occurring at a site selected from the group consisting of (i) one or more of said fatty acid groups being coupled to one or more functional groups of a polyfunctional group which is bound to the N-terminal amino group of the peptide residue,   (ii) one or more of said fatty acid groups being coupled to one or more functional groups of a polyfunctional group which is bound to the C-terminal carboxy group of the peptide residue,   (iii) one of said fatty acid groups being coupled to the N-terminal amino group of the peptide residue and one or more of said fatty acid groups being coupled to one or more functional groups of a polyfunctional group which is bound to the C-terminal carboxy group of the peptide residue, and   (iv) one or more of said fatty acid groups being coupled to one or more functional groups of a polyfunctional group which is bound to the N-terminal amino group of the peptide residue and one or more of said fatty acid groups being coupled to one or more functional groups of a polyfunctional group which is bound to the C-terminal carboxy group of the peptide residue.     
     
     
       2. An antigen according to claim 1, wherein the fatty acid group has 12 to 36 carbon atoms. 
     
     
       3. An antigen according to claim 1, wherein the fatty acid group has 12 to 24 carbon atoms. 
     
     
       4. An antigen according to claim 1, wherein the fatty acid is selected from the group consisting of palmitic acid, stearic acid, behenic acid, oleic acid and mycolic acid. 
     
     
       5. An antigen according to claim 1, wherein the polyfunctional group is a polyamino group. 
     
     
       6. An antigen according to claim 5, wherein the polyamino group is a diamino group. 
     
     
       7. An antigen according to claim 6, wherein one or two or said fatty acid groups is coupled to one or both amino groups of a diamino group which is bound to the N-terminal amino group of the peptide residue. 
     
     
       8. An antigen according to claim 6, wherein one or two or said fatty acid groups is coupled to one or both amino groups of a diamino group which is bound to the C-terminal carboxy group of the peptide residue. 
     
     
       9. An antigen according to claim 6, wherein one of said fatty acid groups is coupled to the N-terminal amino group of the peptide residue and one or two of said fatty acid groups is coupled to one or both amino groups of a diamino group which is bound to the C-terminal carboxy group of the peptide residue. 
     
     
       10. An antigen according to claim 6, wherein one or two of said fatty acid groups is coupled to one or both amino groups of a diamino group which is bound to the N-terminal amino group of the peptide residue and one or two of said fatty acid groups is coupled to one or both amino groups of a diamino group which is bound to the C-terminal carboxy group of the peptide residue. 
     
     
       11. An antigen according to claim 1, wherein the peptide residue is a synthetic peptide. 
     
     
       12. An antigen according to claim 1, wherein the peptide residue comprises an H-epitope of a protein antigen or allergen. 
     
     
       13. An antigen according to claim 6, wherein the diamino group is selected from the group consisting of lysine; ornithine and alpha, gamma diamino butyric acid. 
     
     
       14. A synthetic antigen comprising a carrier coupled to a peptide residue, (a) the peptide residue according to claim 1 additionally having side chain amino groups in addition to an N-terminal amino group, and being coupled to the carrier which comprises   (b) one or more alkyl or alkenyl fatty acid groups having at least 12 carbon atoms, said coupling occurring only at the N-terminal amino group of said peptide residue.   
     
     
       15. An antigen according to claim 14, wherein the fatty acid group has 12 to 36 carbon atoms. 
     
     
       16. An antigen according to claim 14, wherein the fatty acid group has 12 to 24 carbon atoms. 
     
     
       17. An antigen according to claim 14, wherein the alkyl or alkenyl fatty acid group is coupled to the N-terminal amino group of the peptide residue via a carbonyl group. 
     
     
       18. An antigen according to claim 14, wherein the alkyl or alkenyl fatty acid group is coupled directly to the N-terminal amino group of peptide residue. 
     
     
       19. An antigen according to claim 14, wherein the fatty acid is selected from the group consisting of palmitic acid, stearic acid, behenic acid, oleic acid and mycolic acid. 
     
     
       20. An antigen according to claim 14, wherein the peptide residue is a synthetic peptide. 
     
     
       21. An antigen according to claim 14, wherein the peptide residue comprises an H-epitope of a protein antigen or allergen.